Siloxane derivatives of amino acids having surface-active properties
AssigneeAdvanSix Resins & Chemicals LLC
InventorsEdward Asirvatham, Andrei Honciuc, Voichita Mihali
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Abstract
The present disclosure provides siloxane derivatives of amino acids that have surface-active properties. The amino acid can be naturally-occurring or synthetic, or they may be obtained via a ring-opening reaction of a lactam, such as caprolactam. The amino acid may be functionalized with a siloxane group to form a compound that is surface-active and has surfactant characteristics. The compounds have low critical micelle concentrations (CMC) as well as the ability to lower the surface tension of a liquid.
Claims16
A method of synthesizing a siloxane derivative of an amino acid, comprising:
- alkylating an amino end group of 6-aminohexanoic acid to provide a disubstituted amine;
- and
- reacting a carboxyl end group of the disubstituted amine with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative of the amino acid.
A method of synthesizing a siloxane derivative of the Formula I, comprising reacting a carboxyl end group of the following N-alkylated amino acid:
- with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative of the amino acid of the Formula I:
- wherein R1 and R2 may be the same or different, and comprise at least one group selected from the group consisting of C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
- n is an integer from 3 to 12;
- the terminal nitrogen is optionally further substituted with R3, wherein R3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C1-C6 alkyl;
- and
- an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide.
Dependencies are inferred from the claim text.